Fungicidal composition comprising a pyridylethylbenzamide derivative and a compound capable of inhibiting the transport of electrons of the respiratory chain in phytopathogenic fungal organisms

ABSTRACT

A composition comprising at least a pyridylethylbenzamide derivative of general formula (I) (a) and a compound capable of inhibiting the transport of electrons of the respiratory chain in phytopathogenic fungal organisms (b) in a (a)/(b) weight ratio of from 0.01 to 20. A composition further comprising an additional fungicidal compound. A method for preventively or curatively combating the phytopathogenic fungi of crops by using this composition.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a 35 U.S.C. §371 national phase conversion ofPCT/EP2005/002563 filed Feb. 10, 2005, which claims priority of EPApplication No. 04356019.2 filed Feb. 12, 2004, EP Application04356096.0 filed Jun. 11, 2004, and U.S. Provisional Application No.60/637,120 filed Dec. 17, 2004.

The present invention relates to novel fungicide compositions comprisinga pyridylethylbenzamide derivative and a compound capable of inhibitingthe transport of electrons of the respiratory chain in phytopathogenicfungal organisms. The present invention also relates to a method ofcombating or controlling phytopathogenic fungi by applying at a locusinfested or liable to be infested such a composition.

International patent application WO 01/11965 generically disclosesnumerous pyridylethylbenzamide derivatives. The possibility of combiningone or more of these numerous pyridylethylbenzamide derivatives withknown fungicidal products to develop a fungicidal activity is disclosedin general terms, without any specific example or biological data.

It is always of high-interest in agriculture to use novel pesticidalmixtures showing a synergistic effect in order notably to avoid or tocontrol the development of resistant strains to the active ingredientsor to the mixtures of known active ingredients used by the farmer whileminimising the doses of chemical products spread in the environment andreducing the cost of the treatment.

We have now found some novel fungicidal compositions which possess theabove mentioned characteristics.

Accordingly, the present invention relates to a composition comprising:

a) a pyridylethylbenzamide derivative of general formula (I)

in which:

p is an integer equal to 1, 2, 3 or 4;

q is an integer equal to 1, 2, 3, 4 or 5;

each substituent X is chosen, independently of the others, as beinghalogen, alkyl or haloalkyl;

each substituent Y is chosen, independently of the others, as beinghalogen, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, amino, phenoxy,alkylthio, dialkylamino, acyl, cyano, ester, hydroxy, aminoalkyl,benzyl, haloalkoxy, halosulphonyl, halothioalkyl, alkoxyalkenyl, alkylsulphonamide, nitro, alkylsulphonyl, phenylsulphonyl or benzylsulphonyl;

and the N-oxides of the compounds thereof; and

b) a compound capable of inhibiting the transport of electrons of therespiratory chain in phytopathogenic fungal organisms;

in an (a)/(b) weight ratio of from 0.01 to 20.

In the context of the present invention, a compound capable ofinhibiting the transport of electrons of the respiratory chain inphytopathogenic fungal organisms is chosen from the group comprising acompound capable of inhibiting reduced nicotinamide-adenine dinucleotide(NADH) deshydrogenase in phytopathogenic fungal organisms, a compoundcapable of inhibiting succinate dehydrogenase in phytopathogenic fungalorganisms and a compound capable of inhibiting mitochondrialubiquinol:ferricytochrome-c oxidoreductase in phytopathogenic fungalorganisms.

A compound capable of inhibiting NADH dehydrogenase in phytopathogenicfungal organisms is also known as complex I inhibitor.

A compound capable of inhibiting succinate dehydrogenase inphytopathogenic fungal organisms is also known as complex II inhibitor.

A compound capable of inhibiting mitochondrialubiquinol:ferricytochrome-c oxidoreductase in phytopathogenic fungalorganisms is also known as complex III inhibitor.

In the context of the present invention:

-   halogen means chlorine, bromine, iodine or fluorine;-   each of the alkyl or acyl radicals present in the molecule contains    from 1 to 10 carbon atoms, preferably from 1 to 7 carbon atoms, more    preferably from 1 to 5 carbon atoms, and may be linear or branched;-   each of the alkenyl or alkynyl radicals present in the molecule    contains from 2 to 10 carbon atoms, preferably from 2 to 7 carbon    atoms, more preferably from 2 to 5 carbon atoms, and may be linear    or branched.

The composition according to the present invention provides asynergistic effect. This synergistic effect allows a reduction of thechemical substances spread into the environment and a reduction of thecost of the fungal treatment.

In the context of the present invention, the term “synergistic effect”is defined by Colby according to the article entitled “Calculation ofthe synergistic and antagonistic responses of herbicide combinations”Weeds, (1967), 15, pages 20-22.

The latter article mentions the formula:

$E = {x + y - \frac{x*y}{100}}$in which E represents the expected percentage of inhibition of thedisease for the combination of the two fungicides at defined doses (forexample equal to x and y respectively), x is the percentage ofinhibition observed for the disease by the compound (I) at a defineddose (equal to x), y is the percentage of inhibition observed for thedisease by the compound (II) at a defined dose (equal to y). When thepercentage of inhibition observed for the combination is greater than E,there is a synergistic effect.

The composition according to the present invention comprises apyridylethylbenzamide derivative of general formula (I). Preferably, thepresent invention relates to a composition comprising apyridylethylbenzamide derivative of general formula (I) in which thedifferent characteristics may be chosen alone or in combination asbeing:

as regards p, p is 2;

as regards q, q is 1 or 2. More preferably, q is 2;

as regards X, X is chosen, independently of the others, as being halogenor haloalkyl. More preferably, X is chosen, independently of the others,as being a chlorine atom or a trifluoromethyl group;

as regards Y, Y is chosen, independently of the others, as being halogenor haloalkyl. More preferably, Y is chosen, independently of the others,as being a chlorine atom or a trifluoromethyl group;

More preferably, the pyridylethylbenzamide derivative of general formula(I) present in the composition of the present invention is:

-   N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide    (compound 1);-   N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-iodobenzamide    (compound 2); or-   N-{2-[3,5-dichloro-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide    (compound 3).

Even more preferably, the pyridylethylbenzamide derivative of generalformula (I) present in the composition of the present invention isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(compound 1).

The composition according to the present invention comprises a compoundcapable of inhibiting the transport of electrons of the respiratorychain.

Preferably, the present invention also relates to a compositioncomprising a complex I inhibitor. More preferably, the present inventionrelates to a composition comprising a complex I inhibitor which isdiflumetorin.

Preferably, the present invention also relates to a compositioncomprising a complex II inhibitor. More preferably, the presentinvention relates to a composition comprising a complex II inhibitorselected from the carboxamide derivatives which may for example beN-[2-(1,3-dimethyl-butyl)-phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide,N-[2-(1,3-dimethylbutyl)-thiophen-3-yl]1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,benodanil, carboxin, fenfuram, flutolanil, furametpyr, mepronil,boscalid, oxycarboxin, thifluzamide.N-[2-(1,3-dimethyl-butyl)-phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide,boscalid and oxycarboxin are preferred.

Preferably, the present invention also relates to a compositioncomprising a complex III inhibitor. More preferably, the presentinvention relates to a composition comprising a complex III inhibitorselected from strobilurin derivatives, cyazofamid, fenamidone orfamoxadone. Fenamidone is preferred.

Strobilurin derivatives are also preferred. According to the presentinvention, strobilurin derivatives may for example be azoxystrobin,dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin,trifloxystrobin, pyraclostrobin, picoxystrobin or2-{2-[6-(3-chloro-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}2-methoxyimino-N-methylacetamide.2-{2-[6-(3-chloro-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}2-methoxyimino-N-methylacetamide,azoxystrobin, trifloxystrobin and fluoxastrobin are preferred.

The composition according to the present invention comprises (a) atleast a pyridylethylbenzamide derivative of general formula (I) and (b)a compound capable of inhibiting the transport of electrons of therespiratory chain in phytopathogenic fungal organisms in an (a)/(b)weight ratio of from 0.01 to 20; preferably of from 0.05 to 10; evenmore preferably, of from 0.1 to 5.

The composition of the present invention may further comprise at leastone other different fungicide active ingredient (c).

The fungicidal active ingredient (c) may be selected from azaconazole,azoxystrobin,(Z)-N-[α-(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)benzyl]-2-phenylacetamide,6-iodo-2-propoxy-3-propylquinazolin-4(3H)-one, benalaxyl, benomyl,benthiavalicarb, biphenyl, bitertanol, blasticidin-S, boscalid, borax,bromuconazole, bupirimate, sec-butylamine, calcium polysulfide,captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat,chlorothalonil, chlozolinate, copper hydroxide, copper octanoate, copperoxychloride, copper sulfate, cuprous oxide, cyazofamid, cymoxanil,cyproconazole, cyprodinil, dazomet, debacarb, dichlofluanid,dichlorophen, diclobutrazole, diclocymet, diclomezine, dicloran,diethofencarb, difenoconazole, difenzoquat metilsulfate, difenzoquat,diflumetorim, dimethirimol, dimethomorph, diniconazole, dinobuton,dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine,edifenphos, epoxiconazole, ethaboxam, etaconazole, ethirimol,ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fenfuram, fenhexamid, fenpiclonil, fenoxanil,fenpropidin, fenpropimorph, fentin, fentin hydroxide, fentin acetate,ferbam, ferimzone, fluazinam, fludioxonil, fluoroimide, fluoxastrobin,fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol,folpet, formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole,furalaxyl, furametpyr, guazatine, guazatine acetates, hexachlorobenzene,hexaconazole, 8-hydroxyquinoline sulfate, potassium hydroxyquinolinesulfate, hymexazol, imazalil sulfate, imazalil, imibenconazole,iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos,iprodione, iprovalicarb, isoprothiolane, kasugamycin, kasugamycinhydrochloride hydrate, kresoxim-methyl, mancopper, mancozeb, maneb,mepanipyrim, mepronil, mercuric chloride, mercuric oxide, mercurouschloride, metalaxyl, metalaxyl-M, metam-sodium, metam, metconazole,methasulfocarb, methyl isothiocyanate, metiram, metominostrobin,mildiomycin, myclobutanil, nabam, nickel bis(dimethyldithiocarbamate),nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid,oxadixyl, oxine-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate,penconazole, pencycuron, pentachlorophenol, sodium pentachlorophenoxide,pentachlorophenyl laurate, phenylmercury acetate, sodium2-phenylphenoxide, 2-phenylphenol, phosphorous acid, phthalide,picoxystrobin, piperalin, polyoxinspolyoxin B, polyoxin, polyoxorim,probenazole, prochloraz, procymidone, propamocarb hydrochloride,propamocarb, propiconazole, propineb, prothioconazole, pyraclostrobin,pyrazophos, pyributicarb, pyrifenox, pyrimethanil, pyroquilon,quinoxyfen, quintozene, silthiofam, simeconazole, spiroxamine, sulfur,tar oils, tebuconazole, tecnazene, tetraconazole, thiabendazole,thifluzamide, thiophanate-methyl, thiram, tolclofos-methyl,tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole,tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,validamycin, vinclozolin, zineb, ziram and zoxamide.

Preferably, fungicidal active ingredient (c) is selected from captane,folpet, dodine, propineb, mancozeb, thiram, tolylfluanid, iminoctadine,dithianon, copper hydroxide, copper octanoate, copper oxychloride,copper sulfate, fosetyl-Al, phosphorous acid, cymoxanil, iprovalicarb,benthiavalicarb, chlorotalonil, propamocarb, prothioconazole,tebuconazole and spiroxamine.

Where the third active ingredient (c) as defined above is present in thecomposition, this compound may be present in an amount of (a):(b):(c)weight ratio of from 1:0.01:0.01 to 1:20:20; the ratios of compound (a)and compound (c) varying independently from each other. Preferably, the(a):(b):(c) weight ratio may be of from 1:0.05:0.05 to 1:10:10.

Following compositions may be cited to illustrate in a non-limitedmanner the present invention: compound 1 with diflumetorin, compound 1withN-[2-(1,3-dimethyl-butyl)-phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,compound 1 withN-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide,compound 1 withN-[2-(1,3-dimethylbutyl)-thiophen-3-yl]1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,compound 1 with benodanil, compound 1 with carboxin, compound 1 withfenfuram, compound 1 with flutolanil, compound 1 with furametpyr,compound 1 with mepronil, compound 1 with boscalid, compound 1 withoxycarboxin, compound 1 with thifluzamide, compound 1 with cyazofamid,compound 1 with fenamidone, compound 1 with famoxadone. azoxystrobin,compound 1 with dimoxystrobin, compound 1 with fluoxastrobin, compound 1with kresoxim-methyl, compound 1 with metominostrobin, compound 1 withtrifloxystrobin, compound 1 with pyraclostrobin, compound 1 withpicoxystrobin, compound 1 with2-{2-[6-(3-chloro-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}2-methoxyimino-N-methylacetamide,compound 2 with diflumetorin, compound 2 withN-[2-(1,3-dimethyl-butyl)-phenyl]-5-fluoro-1,3-dime-thyl-1H-pyrazole-4-carboxamide,compound 2 withN-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide,compound 2 withN-[2-(1,3-dimethylbutyl)-thiophen-3-yl]1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,compound 2 with benodanil, compound 2 with carboxin, compound 2 withfenfuram, compound 2 with flutolanil, compound 2 with furametpyr,compound 2 with mepronil, compound 2 with boscalid, compound 2 withoxycarboxin, compound 2 with thifluzamide, compound 2 with cyazofamid,compound 2 with fenamidone, compound 2 with famoxadone. azoxystrobin,compound 2 with dimoxystrobin, compound 2 with fluoxastrobin, compound 2with kresoxim-methyl, compound 2 with metominostrobin, compound 2 withtrifloxystrobin, compound 2 with pyraclostrobin, compound 2 withpicoxystrobin, compound 2 with2-{2-[6-(3-chloro-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}2-methoxyimino-N-methylacetamide,compound 3 with diflumetorin, compound 3 withN-[2-(1,3-dimethyl-butyl)-phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,compound 3 withN-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide,compound 3 withN-[2-(1,3-dimethylbutyl)-thiophen-3-yl]1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,compound 3 with benodanil, compound 3 with carboxin, compound 3 withfenfuram, compound 3 with flutolanil, compound 3 with furametpyr,compound 3 with mepronil, compound 3 with boscalid, compound 3 withoxycarboxin, compound 3 with thifluzamide, compound 3 with cyazofamid,compound 3 with fenamidone, compound 3 with famoxadone. azoxystrobin,compound 3 with dimoxystrobin, compound 3 with fluoxastrobin, compound 3with kresoxim-methyl, compound 3 with metominostrobin, compound 3 withtrifloxystrobin, compound 3 with pyraclostrobin, compound 3 withpicoxystrobin, compound 3 with2-{2-[6-(3-chloro-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}2-methoxyimino-N-methylacetamide.

The composition according to the present invention may further comprisean other additional component such as an agriculturally acceptablesupport, carrier or filler.

In the present specification, the term “support” denotes a natural orsynthetic, organic or inorganic material with which the active materialis combined to make it easier to apply, notably to the parts of theplant. This support is thus generally inert and should be agriculturallyacceptable. The support may be a solid or a liquid. Examples of suitablesupports include clays, natural or synthetic silicates, silica, resins,waxes, solid fertilisers, water, alcohols, in particular butanol,organic solvents, mineral and plant oils and derivatives thereof.Mixtures of such supports may also be used.

The composition may also comprise other additional components. Inparticular, the composition may further comprise a surfactant. Thesurfactant can be an emulsifier, a dispersing agent or a wetting agentof ionic or non-ionic type or a mixture of such surfactants. Mention maybe made, for example, of polyacrylic acid salts, lignosulphonic acidsalts, phenolsulphonic or naphthalenesulphonic acid salts,polycondensates of ethylene oxide with fatty alcohols or with fattyacids or with fatty amines, substituted phenols (in particularalkylphenols or arylphenols), salts of sulphosuccinic acid esters,taurine derivatives (in particular alkyl taurates), phosphoric esters ofpolyoxyethylated alcohols or phenols, fatty acid esters of polyols, andderivatives of the above compounds containing sulphate, sulphonate andphosphate functions. The presence of at least one surfactant isgenerally essential when the active material and/or the inert supportare water-insoluble and when the vector agent for the application iswater. Preferably, surfactant content may be comprised between 5% and40% by weight of the composition.

Additional components may also be included, e.g. protective colloids,adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active materialscan be combined with any solid or liquid additive, which complies withthe usual formulation techniques.

In general, the composition according to the invention may contain from0.05 to 99% (by weight) of active material, preferably 10 to 70% byweight.

Compositions according to the present invention can be used in variousforms such as aerosol dispenser, capsule suspension, cold foggingconcentrate, dustable powder, emulsifiable concentrate, emulsion oil inwater, emulsion water in oil, encapsulated granule, fine granule,flowable concentrate for seed treatment, gas (under pressure), gasgenerating product, granule, hot fogging concentrate, macrogranule,microgranule, oil dispersible powder, oil miscible flowable concentrate,oil miscible liquid, paste, plant rodlet, powder for dry seed treatment,seed coated with a pesticide, soluble concentrate, soluble powder,solution for seed treatment, suspension concentrate (flowableconcentrate), ultra low volume (ulv) liquid, ultra low volume (ulv)suspension, water dispersible granules or tablets, water dispersiblepowder for slurry treatment, water soluble granules or tablets, watersoluble powder for seed treatment and wettable powder.

These compositions include not only compositions which are ready to beapplied to the plant or seed to be treated by means of a suitabledevice, such as a spraying or dusting device, but also concentratedcommercial compositions which must be diluted before they are applied tothe crop.

The fungicidal compositions of the present invention can be used tocuratively or preventively control phytopathogenic fungi of crops. Thus,according to a further aspect of the present invention, there isprovided a method for preventively or curatively controllingphytopathogenic fungi of crops characterised in that a fungicidalcomposition as hereinbefore defined is applied to the seed, the plantand/or to the fruit of the plant or to the soil in which the plant isgrowing or in which it is desired to grow.

The composition as used against phytopathogenic fungi of crops comprisesan effective and non-phytotoxic amount of an active material of generalformula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention which is sufficient to control ordestroy the fungi present or liable to appear on the crops, and whichdoes not entail any appreciable symptom of phytotoxicity for the saidcrops. Such an amount can vary within a wide range depending on thefungus to be combated or controlled, the type of crop, the climaticconditions and the compounds included in the fungicidal compositionaccording to the invention.

This amount can be determined by systematic field trials, which arewithin the capabilities of a person skilled in the art.

The method of treatment according to the present invention is useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the present invention can also be useful totreat the overground parts of the plant such as trunks, stems or stalks,leaves, flowers and fruits of the concerned plant.

Among the plants that can be protected by the method according to theinvention, mention may be made of cotton; flax; vine; fruit crops suchas Rosaceae sp. (for instance pip fruits such as apples and pears, butalso stone fruits such as apricots, almonds and peaches), Ribesioidaesp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp.,Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceaesp. (for instance banana trees and plantins), Rubiaceae sp., Theaceaesp., Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges andgrapefruits); leguminous crops such as Solanaceae sp. (for instancetomatoes), Liliaceae sp., Asteraceae sp. (for instance lettuces),Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp.,Papilionaceae sp. (for instance peas), Rosaceae sp. (for instancestrawberries); big crops such as Graminae sp. (for instance maize,cereals such as wheat, rice, barley and triticale), Asteraceae sp. (forinstance sunflower), Cruciferae sp. (for instance colza), Papilionaceaesp. (for instance soja), Solanaceae sp. (for instance potatoes),Chenopodiaceae sp. (for instance beetroots); horticultural and forestcrops; as well as genetically modified homologues of these crops.

Among the plants and the possible diseases of these plants protected bythe method according to the present invention, mention may be made of:

wheat, as regards controlling the following seed diseases: fusaria(Microdochium nivale and Fusarium roseum), stinking smut (Tilletiacaries, Tilletia controversa or Tilletia indica), septoria disease(Septoria nodorum) and loose smut;

wheat, as regards controlling the following diseases of the aerial partsof the plant: cereal eyespot (Tapesia yallundae, Tapesia acuiformis),take-all (Gaeumannomyces graminis), foot blight (F. culmorum, F.graminearum), black speck (Rhizoctonia cerealis), powdery mildew(Erysiphe graminis forma specie tritici), rusts (Puccinia striiformisand Puccinia recondita) and septoria diseases (Septoria tritici andSeptoria nodorum);

wheat and barley, as regards controlling bacterial and viral diseases,for example barley yellow mosaic;

barley, as regards controlling the following seed diseases: net blotch(Pyrenophora graminea, Pyrenophora teres and Cochliobolus sativus),loose smut (Ustilago nuda) and fusaria (Microdochium nivale and Fusariumroseum);

barley, as regards controlling the following diseases of the aerialparts of the plant: cereal eyespot (Tapesia yallundae), net blotch(Pyrenophora teres and Cochliobolus sativus), powdery mildew (Erysiphegraminis forma specie hordei), dwarf leaf rust (Puccinia hordei) andleaf blotch (Rhynchosporium secalis);

potato, as regards controlling tuber diseases (in particularHelminthosporium solani, Phoma tuberosa, Rhizoctonia solani, Fusariumsolani), mildew (Phytopthora infestans) and certain viruses (virus Y);

potato, as regards controlling the following foliage diseases: earlyblight (Alternaria solani), mildew (Phytophthora infestans);

cotton, as regards controlling the following diseases of young plantsgrown from seeds: damping-off and collar rot (Rhizoctonia solani,Fusarium oxysporum) and black root rot (Thielaviopsis basicola);

protein yielding crops, for example peas, as regards controlling thefollowing seed diseases: anthracnose (Ascochyta pisi, Mycosphaerellapinodes), fusaria (Fusarium oxysporum), grey mould (Botrytis cinerea)and mildew (Peronospora pisi);

oil-bearing crops, for example rape, as regards controlling thefollowing seed diseases: Phoma lingam, Alternaria brassicae andSclerotinia sclerotiorum;

corn, as regards controlling seed diseases: (Rhizopus sp., Penicilliumsp., Trichoderma sp., Aspergillus sp., and Gibberella fujikuroi);

flax, as regards controlling the seed disease: Alternaria linicola;

forest trees, as regards controlling damping-off (Fusarium oxysporum,Rhizoctonia solani);

rice, as regards controlling the following diseases of the aerial parts:blast disease (Magnaporthe grisea), bordered sheath spot (Rhizoctoniasolani);

leguminous crops, as regards controlling the following diseases of seedsor of young plants grown from seeds: damping-off and collar rot(Fusarium oxysporum, Fusarium roseum, Rhizoctonia solani, Pythium sp.);

leguminous crops, as regards controlling the following diseases of theaerial parts: grey mould (Botrytis sp.), powdery mildews (in particularErysiphe cichoracearum, Sphaerotheca fuliginea and Leveillula taurica),fusaria (Fusarium oxysporum, Fusarium roseum), leaf spot (Cladosporiumsp.), alternaria leaf spot (Alternaria sp.), anthracnose (Colletotrichumsp.), septoria leaf spot (Septoria sp.), black speck (Rhizoctoniasolani), mildews (for example Bremia lactucae, Peronospora sp.,Pseudoperonospora sp., Phytophthora sp.);

fruit trees, as regards diseases of the aerial parts: monilia disease(Monilia fructigenae, M. laxa), scab (Venturia inaequalis), powderymildew (Podosphaera leucotricha);

vine, as regards diseases of the foliage: in particular grey mould(Botrytis cinerea), powdery mildew (Uncinula necator), black rot(Guignardia biwelli) and mildew (Plasmopara viticola);

beetroot, as regards the following diseases of the aerial parts:cercospora blight (Cercospora beticola), powdery mildew (Erysiphebeticola), leaf spot (Ramularia beticola).

The fungicidal composition according to the present invention may alsobe used against fungal diseases liable to grow on or inside timber. Theterm “timber” means all types of species of wood, and all types ofworking of this wood intended for construction, for example solid wood,high-density wood, laminated wood, and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds of the present invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The fungicidal composition according to the present invention may alsobe used in the treatment of genetically modified organisms with thecompounds according to the invention or the agrochemical compositionsaccording to the invention. Genetically modified plants are plants intoin which genome a heterologous gene encoding a protein of interest hasbeen stably integrated. The expression “heterologous gene encoding aprotein of interest” essentially means genes which give the transformedplant new agronomic properties, or genes for improving the agronomicquality of the transformed plant.

The dose of active material usually applied in the treatment accordingto the present invention is generally and advantageously between 10 and2000 g/ha, preferably between 20 and 1500 g/ha for applications infoliar treatment. The dose of active substance applied is generally andadvantageously between 1 and 200 g per 100 kg of seed, preferablybetween 2 and 150 g per 100 kg of seed in the case of seed treatment. Itis clearly understood that the doses indicated above are given asillustrative examples of the invention. A person skilled in the art willknow how to adapt the application doses according to the nature of thecrop to be treated.

The compositions according to the present invention may also be usedfore the preparation of composition useful to curatively or preventivelytreat human and animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp. or Candida spp., for example Aspergillus fumigatus orCandida albicans respectively.

The present invention will now be illustrated with the followingexamples:

EXAMPLE 1 Efficacy Against Pyrenophora teres of a Composition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and trifloxystrobin

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Barley plants (Express variety) in starter cups, sown on a 50/50 peatsoil-pozzolana substrate and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove. Plants, used as controls, are treated with an aqueous solutionnot containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Pyrenophora teres spores (12 000 spores per ml).The spores are collected from a 12-day-old culture. The contaminatedbarley plants are incubated for 24 hours at about 20° C. and at 100%relative humidity, and then for 12 days at 80% relative humidity.

Grading (% of efficacy) is carried out 12 days after the contamination,in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and trifloxystrobin alone and in a 1/1 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 4 20 — 8 50 —Trifloxystrobin 4 50 — 8 70 — Compound 1 + trifloxystrobin 4 + 4 85 +25(Ratio 1/1) 8 + 8 90  +5

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 2 Efficacy Against Alternaria brassicae (in vitro) of aComposition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and trifloxystrobin

The growth of Alternaria brassicae was followed on PDA medium containingthe compounds alone or in mixtures.

The PDA medium is prepared by mixing 39 grams of PDA (Merck) in 1 litterof demineralised water. The medium is sterilized by autoclave 15 minutesat 121° C. The compounds are dissolved in acetone and added to themedium before pouring it in Petri dishes. After medium drying, thefungus is inoculated on the medium and allowed to growth at 19° C.

The percentage of efficacy is noted after 14 days of growth (measurementof the radial growth) of the fungus in comparison with a control.

The following table summarises the results obtained when tested compound1 and trifloxystrobin alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 0.025 34 — 0.05 45 —0.1 53 — 0.25 76 — 0.5 90 — Trifloxystrobin 0.025 45 — 0.05 44 — 0.1 45— 0.25 53 — 0.5 60 — 1 65 — 2.5 71 — Compound 1 + trifloxystrobin 0.05 +0.05 79 +10 (Ratio 1/1) 0.1 + 0.1 93 +19 0.5 + 0.5 100 +4 Compound 1 +trifloxystrobin 0.05 + 0.1  85 +15 (Ratio 1/2) 0.25 + 0.5  100 +10Compound 1 + trifloxystrobin  0.1 + 0.05 97 +23 (Ratio 2/1)  0.5 + 0.25100 +5 Compound 1 + trifloxystrobin 0.025 + 0.1  75 +11 (Ratio 1/4)Compound 1 + trifloxystrobin  0.1 + 0.025 100 +26 (Ratio 4/1) Compound1 + trifloxystrobin 0.05 + 0.5  96 +18 (Ratio 1/10) 0.25 + 2.5  100 +7

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 3 Efficacy Against Alternaria brassicae (in vitro) of aComposition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and azoxystrobin

The growth of Alternaria brassicae was followed on PDA medium containingthe compounds alone or in mixtures.

The PDA medium is prepared by mixing 39 grams of PDA (Merck) in 1 literof demineralised water. The medium is sterilized by autoclave 15 minutesat 121° C. The compounds are dissolved in acetone and added to themedium before pouring it in Petri dishes. After medium drying, thefungus is inoculated on the medium and allowed to growth at 19° C.

The percentage of efficacy is noted after 14 days of growth (measurementof the radial growth) of the fungus in comparison with a control.

The following table summarises the results obtained when tested compound1 and azoxystrobin alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 0.025 34 — 0.05 45 —0.1 53 — 0.25 76 — 0.5 90 — Azoxystrobin 0.025 38 — 0.05 41 — 0.1 47 —0.25 56 — 0.5 47 — 1 48 — 2.5 49 — Compound 1 + azoxystrobin 0.05 + 0.0570 +2 (Ratio 1/1) 0.1 + 0.1 88 +13 0.5 + 0.5 100 +5 Compound 1 +azoxystrobin 0.05 + 0.1  76 +5 (Ratio 1/2) 0.25 + 0.5  95 +8 Compound1 + azoxystrobin  0.1 + 0.05 81 +9 (Ratio 2/1)  0.5 + 0.25 98 +2Compound 1 + azoxystrobin  0.1 + 0.025 100 +29 (Ratio 4/1) Compound 1 +azoxystrobin 0.05 + 0.5  86 +15 (Ratio 1/10) 0.25 + 2.5  100 +12

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 4 Efficacy Against Erysiphe graminis f. sp. tritici of aComposition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and fluoxastrobin

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Wheat plants (Audace variety) in starter cups, sown on 50/50 peatsoil-pozzolana substrate and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by dusting them withErysiphe graminis f. sp. tritici spores, the dusting being carried outusing diseased plants.

Grading is carried out 7 to 14 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and fluoxastrobin alone and in a 8:1 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 125 20 —Fluoxastrobin  15 20 — Compound 1 + fluoxastrobin 125 + 15 70 +34 (Ratio8/1)

According to the Colby method, a synergistic effect of the mixturetested has been observed.

EXAMPLE 5 Efficacy Against Botrytis cinerea of a Composition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and kresoxim-methyl

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

20 g/L of gelatine

50 g/L of cane sugar

2 g/L of NH4NO3

1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading iscarried out 5 to 7 days after contamination, in comparison with thecontrol plants.

The following table summarises the results obtained when tested compound1 and kresoxim-methyl alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 37 0 — 111 60 — 33390 — Kresoxim-methyl 37 0 — 111 0 — 333 0 — Compound 1 + kresoxim-methyl111 + 111 100 40 (Ratio 1/1) Compound 1 + kresoxim-methyl  37 + 111 9595 (Ratio l/3) 111 + 333 100 40 Compound 1 + kresoxim-methyl  37 + 333100 100 (Ratio 1/9)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 6 Efficacy Against Botrytis cinerea of a Composition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and picoxystrobin

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

20 g/L of gelatine

50 g/L of cane sugar

2 g/L of NH4NO3

1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading iscarried out 5 to 7 days after contamination, in comparison with thecontrol plants.

The following table summarises the results obtained when tested compound1 and picoxystrobin alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 37 0 — 111 60 — 333100 — Picoxystrobin 37 0 — 111 35 — 333 40 — Compound 1 + picoxystrobin111 + 111 95 +21 (Ratio 1/1) Compound 1 + picoxystrobin  37 + 111 90 +55(Ratio 1/3) Compound 1 + picoxystrobin 111 + 37 98 +38 (Ratio 3/1)Compound 1 + picoxystrobin  37 + 333 95 +55 (Ratio 1/9)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 7 Efficacy Against Botrytis cinerea of a Composition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and pyraclostrobin

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

20 g/L of gelatine

50 g/L of cane sugar

2 g/L of NH4NO3

1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading iscarried out 5 to 7 days after contamination, in comparison with thecontrol plants.

The following table summarises the results obtained when tested compound1 and pyraclostrobin alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 12 0 — 37 40 — 111 92— Pyraclostrobin 37 0 — 111 0 — 333 0 — Compound 1 + pyraclostrobin12.3 + 333  100 +100 (Ratio 1/27) Compound 1 + pyraclostrobin  37 + 333100 +60 (Ratio 1/9) 12.3 + 111  85 +85 Compound 1 + pyraclostrobin  37 + 12.3 55 +15 (Ratio 3/1)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 8 Efficacy Against Botrytis cinerea of a Composition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and2-{2-[6-(3-Chloro-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}2-methoxyimino-N-methylacetamide(Compound A)

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

20 g/L of gelatine

50 g/L of cane sugar

2 g/L of NH4NO3

1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading iscarried out 5 to 7 days after contamination, in comparison with thecontrol plants.

The following table summarises the results obtained when tested compound1 and compound A alone and in different weight ratio mixtures.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 37 3 — 111 58 — 33375 — Compound A 37 0 — 111 0 — 333 0 — Compound 1 + compound A 333 + 333100 +25 (Ratio 1/1) 111 + 111 100 +42 Compound 1 + compound A 333 + 111100 +25 (Ratio 3/1) Compound 1 + compound A 111 + 333 100 +42 (Ratio1/3) Compound 1 + compound A  37 + 333 75 +72 (Ratio 1/9)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 9 Efficacy Against Erysiphe graminis f. sp. tritici of aComposition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and dimoxystrobin

The formulated compounds are diluted with water to obtain the desiredactive material concentration.

Wheat plants (Audace variety) in starter cups, sown on 50/50 peatsoil-pozzolana substrate and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by dusting them withErysiphe graminis f. sp. tritici spores, the dusting being carried outusing diseased plants.

Grading is carried out 7 to 14 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and dimoxystrobin alone and in a 1/8 weight ratio mixture.

Dose Synergism (g/ha) % Efficacy (Colby) Compound 1 250 50 —Dimoxystrobin 62.5 0 — Compound 1 + dimoxystrobin 250 + 62.5 95 +45(Ratio 1/8)

According to the Colby method, a synergistic effect of the mixturetested has been observed.

EXAMPLE 10 Efficacy Against Botrytis cinerea of a Composition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) andN-[2-(1,3-dimethyl-butyl)-phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide(Compound B)

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

20 g/L of gelatine

50 g/L of cane sugar

2 g/L of NH4NO3

1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading iscarried out 5 to 7 days after contamination, in comparison with thecontrol plants.

The following table summarises the results obtained when tested compound1 and compound B alone and in a 9/1 weight ratio mixture.

Dose Synergism (ppm) % Efficacy (Colby) Compound 1 37 72 — Compound B 432 — Compound 1 + compound B 37 + 4 100 +19 (Ratio 9/1)

According to the Colby method, a synergistic effect of the mixturetested has been observed.

EXAMPLE 11 Efficacy Against Sphaerotheca fuliginea of a CompositionContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and boscalid

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 20° C./23° C., aretreated at the 2-leaves stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Sphaerotheca fuliginea spores (100 000 spores perml). The spores are collected from a contaminated plants Thecontaminated gherkin plants are incubated at about 20° C./25° C. and at60/70% relative humidity.

Grading (% of efficacy) is carried out 21 days after the contamination,in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and boscalid alone and in a 1/1 weight ratio mixture.

Dose % Synergism (ppm) Efficacy (Colby) Compound 1 4 10 — 8 15 — 15 25 —Boscalid 4 0 — 8 10 — 15 45 — Compound 1 + boscalid 4 + 4 40 +30 (Ratio1/1) 8 + 8 70 +47 15 + 15 95 +36

According to the Colby method, a synergistic effect of the mixturestested has been observed.

EXAMPLE 12 Efficacy Against Sphaerotheca fuliginea of a CompositionContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(compound 1) andN-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide(Compound C)

The active ingredients tested are prepared by potter homogenisation in amixture of acetone/tween/water. The suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 20° C./23° C., aretreated at the 2-leaves stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Sphaerotheca fuliginea spores (100 000 spores perml). The spores are collected from a contaminated plants. Thecontaminated gherkin plants are incubated at about 20° C./25° C. and at60/70% relative humidity.

Grading (% of efficacy) is carried out 21 days after the contamination,in comparison with the control plants.

The following table summarises the results obtained when tested compound1 and compound C alone and in different weight ratio mixtures.

Synergism Dose (ppm) % Efficacy (Colby) Compound 1 31.2 86 — 15.6 18 —7.8 10 — Compound C 62.5 0 — 31.2 0 — Compound 1 + compound C 15.6 +62.5 87 40 (Ratio 1/4) 7.8 + 31  73 25 Compound 1 + compound C  7.8 +62.5 100 59 (Ratio 1/8)

According to the Colby method, a synergistic effect of the mixturetested has been observed.

EXAMPLE 13 Efficacy Against Alternaria brassicae of a CompositionContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1) and fenamidone

The formulated compounds are diluted with water to obtain the desiredactive material concentration.

Radish plants (Pernot variety) in starter cups, sown on a 50/50 peatsoil-pozzolana substrate and grown at 18-20° C., are treated at thecotyledon stage by spraying with the aqueous suspension described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Alternaria brassicae spores (40,000 spores percm³). The spores are collected from a 12-13-day-old culture.

The contaminated radish plants are incubated for 6-7 days at about 18°C., under a humid atmosphere.

Grading is carried out 6 to 7 days after the contamination, incomparison with the control plants.

The following table summarises the results obtained when tested compound1 and fenamidone alone and in a 1/27 weight ratio mixture.

Dose % Synergism (ppm) Efficacy (Colby) Compound 1 4 40 — Fenamidone 11155 — Compound 1 + fenamidone 4 + 111 73 +17 (Ratio 1/27)

According to the Colby method, a synergistic effect of the mixturetested has been observed.

EXAMPLE 14 Efficacy Against Botrytis cinerea of a Composition ContainingN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide(Compound 1)N-[2-(1,3-dimethylbutyl)-thiophen-3-yl]1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide(Compound D)

The formulated compounds are diluted with water to obtain the desiredactive material concentration.

Gherkin plants (Petit vert de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 18-20° C., are treatedat the cotyledon Z11 stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by depositing drops of anaqueous suspension of Botrytis cinerea spores (150,000 spores per ml) onupper surface of the leaves. The spores are collected from a 15-day-oldculture and are suspended in a nutrient solution composed of:

20 g/L of gelatine

50 g/L of cane sugar

2 g/L of NH4NO3

1 g/L of KH2PO4

The contaminated gherkin plants are settled for 5/7 days in a climaticroom at 15-11° C. (day/night) and at 80% relative humidity. Grading iscarried out 5 to 7 days after contamination, in comparison with thecontrol plants.

The following table summarises the results obtained when tested compound1 and compound D alone and in different weight ratio mixtures.

Dose % Synergism (ppm) Efficacy (Colby) Compound 1 31.2 20 — 62.5 40 —Compound D 250 60 — Compound 1 + compound D 31.2 + 250 85 +17 (Ratio8:1) Compound 1 + compound D 62.5 + 250 95 +19 (Ratio 4:1)

According to the Colby method, a synergistic effect of the mixturestested has been observed.

1. A composition comprising: a) a pyridylethylbenzamide derivativeselected from the group consisting of:N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide;N-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-iodobenzamide;and N-{2-[3,5-dichloro-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide;and the N-oxides of 2-pyridine thereof; and b) a compound capable ofinhibiting the transport of electrons of the respiratory chain inphytopathogenic fungal organisms selected from the group consisting of:(1) a compound capable of inhibiting succinate dehydrogenase inphytopathogenic fungal organisms and (2) a compound capable ofinhibiting mitochondrial ubiquinol:ferricytochrome-c oxidoreductase inphytopathogenic fungal organisms; in an (a)/(b) weight ratio of from0.01 to
 20. 2. The composition of claim 1 wherein thepyridylethylbenzamide derivative isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide.3. The composition of claim 1 wherein the compound capable of inhibitingthe transport of electrons of the respiratory chain in phytopathogenicfungal organisms is a compound capable of inhibiting succinatedehydrogenase in phytopathogenic fungal organisms.
 4. The composition ofclaim 3 wherein the compound capable of inhibiting the transport ofelectrons of the respiratory chain of succinate dehydrogenase inphytopathogenic fungal organisms is selected from the group consistingofN-[2-(1,3-dimethyl-butyl)-phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoro-methyl)-1-methyl-1H-pyrazole-4-carboxamide,N-[2-(1,3-dimethylbutyl)-thiophen-3-yl]1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,benodanil, carboxin, fenfuram, flutolanil, furametpyr, mepronil,boscalid, oxycarboxin and thifluzamide.
 5. The composition of claim 1wherein the compound capable of inhibiting the transport of electrons ofthe respiratory chain in phytopathogenic fungal organisms is a compoundcapable of inhibiting mitochondrial ubiquinol:ferricytochrome-coxidoreductase in phytopathogenic fungal organisms.
 6. The compositionof claim 5 wherein the compound capable of inhibiting the transport ofelectrons of the respiratory chain of mitochondrialubiquinol:ferricytochrome-c oxidoreductase in phytopathogenic fungalorganisms is selected from the group consisting of a strobilurinderivative, cyazofamid, fenamidone and famoxadone.
 7. The composition ofclaim 6 wherein the strobilurin derivative is selected from the groupconsisting of azoxystrobin, dimoxystrobin, fluoxastrobin,kresoxim-methyl, metominostrobin, trifloxystrobin, pyraclostrobin,picoxystrobin and2-{2-[6-(3-chloro-2-methylphenoxy)-5-fluoro-pyrimidin-4-yloxy]-phenyl}2-methoxyimino-N-methylacetamide.8. The composition of claim 1 further comprising a fungicidal compound(c).
 9. The composition of claim 8 wherein the fungicidal compound (c)is selected from the group consisting of captane, folpet, dodine,propineb, mancozeb, thiram, tolylfluanid, iminoctadine, dithianon,copper hydroxide, copper octanoate, copper oxychloride, copper sulfate,fosetyl-Al, phosphorous acid, cymoxanil, iprovalicarb, benthiavalicarb,chlorotalonil, propamocarb, prothioconazole, tebuconazole andspiroxamine.
 10. The composition of claim 1 further comprising anagriculturally acceptable support, carrier, filler and/or surfactant.11. The composition of claim 4 wherein the pyridylethylbenzamidederivative isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide.12. The composition of claim 6 wherein the pyridylethylbenzamidederivative isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide.13. The composition of claim 7 wherein the pyridylethylbenzamidederivative isN-{2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-trifluoromethylbenzamide.14. The composition of claim 11 further comprising a fungicidal compound(c) selected from the group consisting of captane, folpet, dodine,propineb, mancozeb, thiram, tolylfluanid, iminoctadine, dithianon,copper hydroxide, copper octanoate, copper oxychloride, copper sulfate,fosetyl-Al, phosphorous acid, cymoxanil, iprovalicarb, benthiavalicarb,chlorotalonil, propamocarb, prothioconazole, tebuconazole andspiroxamine.
 15. The composition of claim 12 further comprising afungicidal compound (c) selected from the group consisting of captane,folpet, dodine, propineb, mancozeb, thiram, tolylfluanid, iminoctadine,dithianon, copper hydroxide, copper octanoate, copper oxychloride,copper sulfate, fosetyl-Al, phosphorous acid, cymoxanil, iprovalicarb,benthiavalicarb, chlorotalonil, propamocarb, prothioconazole,tebuconazole and spiroxamine.
 16. The composition of claim 13 furthercomprising a fungicidal compound (c) selected from the group consistingof captane, folpet, dodine, propineb, mancozeb, thiram, tolylfluanid,iminoctadine, dithianon, copper hydroxide, copper octanoate, copperoxychloride, copper sulfate, fosetyl-Al, phosphorous acid, cymoxanil,iprovalicarb, benthiavalicarb, chlorotalonil, propamocarb,prothioconazole, tebuconazole and spiroxamine.